Citation: Shao Yandong, Wang Xianghui, Xie Lingjie, Men Rui, Lin Qiang. Syntheses and Antibacterial Activities of Erucin Derivatives[J]. Chemistry, ;2016, 79(11): 1058-1062. shu

Syntheses and Antibacterial Activities of Erucin Derivatives

1.
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158

Corresponding author: Wang Xianghui, Lin Qiang,
Received Date: 18 March 2016
Available Online: 30 May 2016
Fund Project:

Ten erucin analogues were synthesized through substitution, aminolysis, and nucleophilic substitution reaction, starting from N-(2-bromoethyl)phthalimide or N-(4-bromobutyl)phthalimide and sodium hydrosulfide. All of synthesized compounds were tested for their antimicrobial activities in vitro by turbidimetric method against Escherichia coli(DH5a), Staphylococcus aureus(ATCC25923), Staphylococcus albus(ATCC8799), Staphylococcus lutea(ACCC11001), Bacillus subtilis(ATCC6633), Bacillus cereus(ACCC11077) and Micrococcus tetragenus(ATCC35098). The results indicated that all compounds exhibit good antimicrobial activities. Benzyl(2-thiocyanatoethyl)sulfane(5e) and benzyl(4-thiocyanatobutyl)sulfane(5j) showed best inhibitory effects against Escherichia coli(DH5a), with the minimum inhibitory concentration(MIC) of 7.8μg/mL, and excellent inhibitory effects against Staphylococcus aureus(ATCC25923), with the MIC of 15.6μg/mL and 31.2μg/mL.
- Erucin,
- Synthesis,
- Antibacterial activity
1. [1]
  [1] R Gmelin, M Schlüter. Arch. Pharm., 1970, 303(4):330~334.
2. [2]
  [2] G Garg, V Sharma. J. Herbs Spic. Med. Plants, 2014, 20(2):171~182.
3. [3]
  [3] C Herz, A Hertrampf, S Zimmermann et al. J. Cell. Mol. Med., 2014, 18(12):2393~2403.
4. [4]
  [4] A Martínez-Sánchez, A Gil-Izquierdo, M I Gil et al. J. Agric. Food Chem., 2008, 56(7):2330~2340.
5. [5]
  [5] A Melchini, C Costa, M Traka et al. Food Chem. Toxicol., 2009, 47(7):1430~1436.
6. [6]
  [6] N Kuhnert, B Holst, G Williamson. J. Labelled Compd. Radiopharm., 2001, 44(5):347~354.
7. [7]
  [7] M Vermeulen, B Zwanenburg, G J F Chittenden et al. Eur. J. Med. Chem., 2003, 38(7~8):729~737.
8. [8]
  [8] H Ganin, J Rayo, N Amara et al. MedChemComm, 2013, 4(1):175~179.
9. [9]
  [9] K Hu, Y Qi, J Zhao et al. Eur. J. Med. Chem., 2013, 64:529~539.
10. [10]
  [10] Q Yu, R Tsao, M Chiba et al. J. Food Agric. Environ., 2005, 3(2):218~221.
11. [11]
  [11] H Wu, X Zhang, G Zhang et al. J. Phytopathol., 2011, 159(6):450~455.
12. [12]
  [12] A E Wilson, M Bergaentzléa, F Bindler et al. Food Contr., 2013, 30(1):318~324.
13. [13]
  [13] C Fimognari, E Turrini, L Ferruzzi et al. Mutat. Res., 2012, 750(2):107~131.
14. [14]
  [14] J Baddiley, E M Thain. J. Chem. Soc., 1951:2253~2258.
15. [15]
  [15] Y Sato, H Nakai, M Wada et al. Eur. J. Org. Chem., 1985(6):1099~1118.
16. [16]
  [16] 胡昌勤, 刘炜. 抗生素微生物检定法及其标准操作. 北京:气象出版社, 2004:1~30.
17. [17]
  [17] M W Tsao, C L Hoffmann, J F Rabolt et al. Langmuir, 1997, 13(16):4317~4322.
18. [18]
  [18] C Bieniarz, M J Cornwell. Tetrahed. Lett., 1993, 34(6):939~942.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
4. [4]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
7. [7]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
10. [10]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
11. [11]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
12. [12]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
13. [13]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
14. [14]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
15. [15]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
16. [16]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
17. [17]
  Ye Wang , Ruixiang Ge , Xiang Liu , Jing Li , Haohong Duan . An Anion Leaching Strategy towards Metal Oxyhydroxides Synthesis for Electrocatalytic Oxidation of Glycerol. Acta Physico-Chimica Sinica, 2024, 40(7): 2307019-0. doi: 10.3866/PKU.WHXB202307019
18. [18]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
19. [19]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
20. [20]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(423)
HTML views(50)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142